This is the first in a blog series focusing on the skills required for headship in today’s changing world.

Recently I was sitting out on my porch looking out on the Okatie River and catching up with an old friend. I was in the first days of recovering from a May orthopedic procedure that would keep me off my feet and housebound for the month of June waiting for literal marching orders from my doctor. From this procedure and considerable travel beforehand, my blog writing had taken a holiday as I pushed through the late spring, getting increasingly comfortable with my inner consultant, so to speak. However, having this chance to “talk shop” was a welcome break from the daily routine of recovery—watching the tide rise and fall on the Okatie River—and our conversation stimulated this blog offering—and the series to follow.

Having taught together at The Taft School for several years in the late 70’s and early 80’s, Jim Mooney and I had followed similar paths from Connecticut. We both accepted headships in the 90’s—I in New Jersey and Jim in Vermont—and enjoyed (if you can call it that) fairly long tenures into the new century. However, Jim left headmastering several years before I stepped down from Blair, going on to become the Deputy Director for a large multi-state independent school organization. One of his primary responsibilities has been overseeing school accreditation, a role that allowed Jim the opportunity to visit with hundreds of schools and examine their cultures, their successes and challenges. In doing so, he has also gained a sense of the strengths and weaknesses associated with school leadership---an area in which I am particularly interested and about which we talked for several hours.

The Transition Surge

Jim offered his assessment of independent school health and progress, but especially his analysis on the present state of school headship. In the course of our talk, Jim threw out a surprising statistic: in the next five years around 1,000 headships at independent schools will turn over.

Around a thousand?

Well, he said, more specifically around two hundred a year. Further, 70% of this change is generational; one group of leaders moves on making room the new group.

Right.

Except one thing, he went on. Only around 20% of present administrators—the group from which the leadership traditionally comes—is interested in being a head of school. Big gap, eh? I can’t say I fully understand it, but there is a serious de-coupling between the leaving heads and the rising aspirants.

I must have given Jim an incredulous look, so he went on to offer his opinion on the most likely three reasons for this looming era of leadership uncertainty:

a. The much larger than usual generational shift of retiring heads of school

b. The trepidation among potential aspirants that failed headships are more common

c. The realization that schools are seeing rise in leadership complexity, the diverse management tasks involved, and relentless time expectations associated with being a head

And of the three reasons, which is most in play? Jim had a ready and thoughtful answer. Well, oddly, it is not letter ‘a.’ There is a generational shift, of course, but I see the issue as a significant cultural shift in school leadership. And we are learning that the old progression of a good administrator—or even promising teacher—moving up and into a headship is not a high percentage model for success. Of course, some independent school professionals still want to be heads of school, and some are good, but the role is now so challenging, accessible preparation so thin, and boards so demanding that many new heads seem doomed to disappoint, be unhappy, or simply fail. Consequently, search committees are looking outside of the traditional candidate pools for fresh leadership. But even if the committees find a great choice, successful heads seem to wear down sooner than they used to. I think generally, most consultants say internationally schools transition leadership in three to five years. Nationally around six to eight.

I told him that these are issues about which, since leaving my headship, I had been mulling over. There is little dispute that school search committees and the constituents they represent want certain qualities in their school leaders: integrity, confidence, and vision. School communities want and need to be inspired, want to trust leadership, and want to respect the head of school. National surveys of the qualities sought in educational leaders continue to reflect that faculty, students, parents, and trustees are eager to follow that forward-thinking, trustworthy woman or man at the top, particularly if that person can articulate in word and manner the aspirational vision the school seeks. Yet, that same head of school, no matter how admirable his or her values, must avoid the trap of playing the traditional role of unilateral leadership—head of school as the one person in charge of everything.

The Real Work of Leadership

In reality admirable personal qualities do not predict some facile translation into leadership competence. To be sure, it is difficult in the search process to separate the desired character qualities communities like to see embodied in their choice of leader from the managerial skill necessary to oversee the complex daily functioning of an educational community. In my opinion, and what I said to Jim, is that we should be exploring this disconnect between leadership character—the abstract and ideal qualities we all admire—and the deft, thoughtful, responsive managerial skill necessary to make educational community.

I asked Jim what areas have most significantly changed since he and I had been teaching together in the 70’s. Jim felt that two areas were particular catalysts behind the complexity in school leadership: the rise of technology and the demand of institutional advancement. Further, those two factors in increasing management demands create a third factor: the necessity for a larger and more talented administrative team than might have been the case twenty years ago. (And we know that larger administrative costs are behind the sharp rise in expense in all levels of education.)

With the first issue, a school’s infrastructure and culture have together had to ramp up significantly over last two decades to manage and respond to the surge of information/expectation aligned with 24/7 connectivity. Every office and nearly all adults—not to go into student technology issues—have to manage daily the need to respond, to manage, to put in perspective daily information flow. And for the head of school and school administrations generally, the remarkable variety of challenges and opportunities that technology presents has raised the bar on management complexity.

I mentioned the impact of relentless press for “school advancement” administrative growth and strategic planning demands; and together those forces influence the pressure of higher-than-inflation cost for which world of education is now in the spotlight. Asking if Jim had noticed the tension between cost containment/budget management during your last years as headmaster, I told him, good luck. The variety of services and high outcomes expectations that our lofty tuitions create is directly connected to management complexity. Today’s independent schools (and colleges for that matter) have to reflect both the facility resources and human responsiveness and oversight well beyond what the world expected twenty years ago. For example, when Jim and I started teaching in the1970’s, older students played a responsible role in school management; today, of course, such a model would be an unacceptable liability.

Finally, to manage not only these two issues but also the entirety of a school culture requires a “deep bench” administration, a group of men and women who collaborate and communicate well, but have the confidence and support to act independently and decisively to complement a successful administrative culture. It is, of course, an expectation of the head to develop, train, nurture and manage this deep bench culture, even as she/he knows that in a world of strong school leadership needs—1,000 headships opening up in five years—that bench could be periodically picked off and need to be re-built. Even if fewer administrators want to be heads, there are many upper administrative roles to fill and moving from a lower role to a major role is one way to advance.

Three Top Competencies for Headship

Deeper into our conversation on the subject, we pursued the topic of management challenges that current and future leaders face to be successful in moving an educational community forward: as Jim said, a successful leader does not rise from bed and say, “I am going to have an integrity day.” Rather each day a head of school does wake to a constantly churning mental checklist of issues to which, and people to whom, attention must be paid. And how well that list gets composed, managed and checked, often reflects how the big picture issues get accomplished: the success of the apparent little things is directly related to the ultimate success of the community as a whole. Still, if they expect competent daily management, then boards of trustees must collaborate with the head on the big picture issues and take some strategic tasks off the head of school’s plate.

In the end, we came up with three critical areas of pro-active, focused competency necessary for a head of school to enjoy a successful tenure—and even that is, if things beyond his or her control go reasonably well. The list could be considerably longer, but for the sake of this blog, here are the top three competencies of today’s successful school leader.

1. Communication

2. Inclusion

3. Decisiveness

We talked about each of these traits, both in terms of formulating effective habits of conduct and in terms of the most common examples of poor performance in each area. And, thus, to give these separate important skills their proper due, I want to follow this introductory blog with three short discussions on each one and a wrap up on the whole issue of dependable, consistent leadership.